


Dean and the Pink Panties

by BuckyBarn3s



Series: Supernatural One Shots [9]
Category: Supernatural
Genre: F/M, Other, Panties, trans woman
Language: English
Status: Completed
Published: 2020-12-27
Updated: 2020-12-26
Packaged: 2021-03-11 06:53:54
Rating: Teen And Up Audiences
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 2
Words: 1,008
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28347210
Author URL: https://archiveofourown.org/users/BuckyBarn3s/pseuds/BuckyBarn3s
Relationships: Rhonda Hurley/Dean Winchester
Series: Supernatural One Shots [9]
Series URL: https://archiveofourown.org/series/2075940
Kudos: 3





	1. Chapter One

Dean was nineteen, hustling pool at some local bar. Sammy was going to get hungry and Dean needed to make sure the kid could eat, especially with his sudden growth spurt. Wouldn't be long and he would be taller than Dean himself. Dean finished off the poor guy he was playing with and gathered up his cash to pocket. He wouldn't be able to make any more cash this way tonight, since everyone paying attention knew that he could actually play, so Dean decided to mingle for a bit, hoping for someone to get laid with tonight. A tall young woman caught his eye from the corner of the bar. She was eyeing him with this blatant "Come hither" look. She was pretty, with her South of the Border skin and black hair that cascaded down her back in waves. Her eyes were heavily lined, enough so he could see them from the distance. He decided he better go over there if he wanted to get on top of this, or her.

"How're you, malady?" Dean asked, all charm and perfect teeth.

"Better now that you're here, baby," she said as her hand found Dean's arm.

"What do ya say we find a more private place?" Dean asked. No point in beating around the bush, right?

"Sure thing, got a car?"

"Yes, ma'am." Boy, he was certainly laying it on thick tonight. He led the way to his pride and joy, a black four door 1967 Chevrolet Impala. A beauty, and in pristine shape. She was gorgeous.

***

"Just try them on, baby, I know you'll like them." Rhonda encouraged, her own black satin panties strained with a bulging cock.

"I don't know, maybe I should just go." But here's the problem, Dean was intrigued and didn't want to leave. He genuinely wondered what it would be like to feel that satin on his cock, rubbing and stretching. "Do they have to be pink?"

"You won't be any less a man, and, baby, you are all man, if you wear pink panties."

"Fine," Dean pouted as he slid the smooth satin over his hairy legs. There wasn't really any room for his cock, but he did have to admit, they felt pretty damned good.

"See, told you it was nice," Rhonda said, smiling seductively as she advanced and ran long nails over the satin enclosed cock. "Now what do you say we have a little fun?"


	2. Chapter Two

When Rhonda and Dean had finished their little sexcapade, Dean was dressing to leave. He had taken off the panties and was about to drop them in the dirty clothes hamper in the corner when Rhonda told him he could keep them. He was sorely tempted, but what if Dad found them? Or worse, Sammy?

"I couldn't keep them."

"Sure you can. If anyone asks why you have a pair of panties just tell them it was from one of your conquests, you wouldn't exactly be lying." Rhonda offered intelligent advice, but still... could he take these underwear? True there was not really any room for his cock to rest comfortably, but the fabric was so smooth and just plain felt amazing against his skin. Was that reason enough to keep them? Sure it was. So Dean pocketed the panties and said his thanks before taking his leave.

He could feel the pressure of the underwear in his pocket as he walked out to his car and drove home. It was as if they weighed over a hundred pounds when they didn't even come close to one pound. He knew eventually Sammy or Dad was going to find the underwear. No doubt, but if he could put off the inevitable for longer, he would. The best way to hide them would be to wear them. So he was going to wear them anytime Dad was around. Dean's pants were always above his underwear and his shirts always extended past the rim of his jeans, so he was covered. And he could create a little pocket in his duffel where he could stash them.

He really should just throw them out the window, for all the mental strife it was causing him, but he couldn't make himself do it. He had to keep them, even if it was for a momento of the time he had sex with a male to female preop transgender. At least, that's what Dean remembers her saying.

***

TWENTY YEARS LATER

Dean opens up his top drawer in his Men of Letters bedroom. He opens up the false bottom and finds the pink underwear he was given about twenty years ago. Every once in a while he gets these out and has to put them on. He has to play with himself wearing them. He's bought more over the years, blue, green, purple, black, virgin white, and so many other colors, but never has he bought another pink pair. That color has a strong meaning for him and there can never be another pair to replace the ones in his hands. Sometimes he looks Rhonda Hurley up to see how she's doing. She's had the bottom surgery, and is married to a nice enough looking young man. Sometimes he wonders if Rhonda remembers him. But it doesn't really matter. He has the underwear and the memory of her.

***  
RHONDA

She kept it all these years. She often wonders why Dean hadn't noticed, or maybe he did. She'll never know. But she kept his wallet that night, thinking maybe he'd realize it and come back for it, just so she could have some more wild sex with him. But he never did. She couldn't ever find any mention of him anywhere, and she gave up when she saw in the news the he was dead. Hard to believe she'd fucked a man who was a grave desecrator and someone who breaks and enters and a whole slew of other nefarious activities. But now he was dead, and she might as well keep the momento of one of her favorite nights ever.


End file.
